Synthesis of 2-acyl-3-methylthiofurans from 3-methylthio-2-pentene-1,5-dione enolates

2-Acyl-3-methylthiofurans 3 are obtained in fair yields from 3-methylthio-2-pentene-1,5-dione enolates 1 by reaction with iodine. In a similar reaction 1-phenyl-3-methylthio-4-nitro-2-buten-1-one gave 3-methylthio-2-nitro-5-phenylfuran 11. In the crystalline state the 2-benzoyl-3-methylthio-5-phenylfuran 3b showed a non-bonded sulfur-oxygen interaction as inferred from an X-ray diffraction determination, with a S····O distance of 2.871(5)Å.